I spent a week in Lakeside, Michigan with my fiancé and another couple. The plan was simple. Stay near Lake Michigan to enjoy “Lake Life” and keep things flexible.

Lakeside worked well as a base. It’s quiet but close to everything. We moved between New Buffalo, South Haven, and Saugatuck without spending much time driving.

Getting In and Starting in Three Oaks

We got into the rental and went straight to Journeyman Distillery in Three Oaks. Easy way to settle into the trip after the flight.

We ordered a few drinks and snacks and really enjoyed our visit. The Aviation stood out. Light, slightly floral, not too sweet.

Beach Days and Coffee Stops

The first full day was at the beach.

Trending

Porto, Portugal: Four Days of Tiles, Tarts, and Tawny Port

Lake Michigan exceeded my expectations. It truly was more like an ocean than a lake. Tides, waves, and the shoreline is wide and open, and it’s easy to spend hours there without noticing.

Our rental was near Whistle Stop Grocery, often on the way to/from the lake, we would grab an iced coffee and pick up something for lunch. That became part of the routine. Most days included at least one stop, sometimes two.

South Haven Day Trip

We spent a full day exploring South Haven, and it ended up being one of those places that’s easy to fall into without a plan. The town sits right along Lake Michigan, so everything feels relaxed—walkable streets, boats coming in and out of the harbor, and that constant lake breeze that makes you want to stay outside all day.

We started with lunch at Admiral Jack’s, right on the water. It’s the kind of spot where you can sit back, watch boats drift by, and lose track of time between bites. From there, we wandered through downtown, popping into shops and just taking in the pace of the town.

A mid-afternoon stop at Biggby Coffee gave us a quick reset—strong coffee, something sweet, and a chance to slow down before heading back out.

We wrapped up the day at New Holland Brewing Company, which added a different energy to the afternoon. Located right in downtown, it’s a great place to settle in with a drink and soak in the atmosphere after a full day of exploring, especially with their focus on handcrafted spirits and cocktails.

Dinner in New Buffalo

Since New Buffalo was close to where we were staying, We drove over for three different dinners.

One of our first stops was The Stray Dog Bar & Grill, which is easily one of the most popular spots in town. Sitting up on the rooftop with views of Lake Michigan, it felt like the perfect place to kick off the evening. The atmosphere leaned lively and casual, with a menu full of crowd-pleasers—burgers, sandwiches, and drinks that pair well with a sunset view.

For something a little more elevated, we had dinner at Terrace Room. The setting here was quieter and more refined, making it a nice contrast to the busier spots around town.

We also made a stop at Brewster’s Italian Cafe, which brought a completely different vibe. Cozy and classic, it felt like a go-to neighborhood spot. The menu focused on comforting Italian dishes—simple, familiar, and exactly what you want after a full day near the lake.

Between the three, New Buffalo delivered a really well-rounded food scene—laid-back rooftop views, upscale dining, and comforting classics all within a few minutes of each other.

Saugatuck Day Trip

One evening, we made the short drive over to Saugatuck, which had a slightly more lively, artsy feel compared to the other towns. We started with dinner at Pumpernickel’s Eatery, where we went the small plates route—bao buns, seafood pasta, and a couple of cocktails that made it easy to settle in and take our time.

After dinner, we wandered through town, popping into a few shops and just enjoying the energy of the area as the evening picked up.

We wrapped it all up with ice cream from Charlie’s Round the Corner Ice Cream, which felt like the perfect low-key ending to the night.

Boat Day on Lake Michigan

One of the best days of the trip was spent out on Lake Michigan, and it ended up being one of those days where everything just lined up perfectly. Clear skies, calm water, and just enough breeze to make being out on the lake feel effortless.

We started in Saugatuck and cruised north along the shoreline, passing stretches of beach, dunes, and lakefront homes that all look even better from the water. There’s something about seeing this part of Michigan by boat that completely changes the perspective—it feels quieter, more open, and a little removed from everything else.

We made our way toward Holland and docked for lunch, which broke up the day perfectly. Being able to hop off the boat, grab food, and then head right back out made the whole experience feel easy and unstructured—in the best way.

Best Dinner of the Trip: Gather in South Haven

One of the best meals of the trip was at Gather, and it ended up being the kind of dinner where everything just kept getting better with each dish. We started with drinks—the empress gimlet and a peach margarita were both standout choices—alongside a pimento cheese dip that set the tone right away.

From there, the table quickly filled with a mix of small plates and mains: a fresh peach and burrata salad, roasted zucchini, and crispy smashed potatoes that were impossible not to keep going back to.

The entrées carried that momentum, with steak frites and salmon with dill both perfectly done, plus a rich mac and cheese that easily held its own. Somewhere in between, a gin fizz and a beer made their way into the mix, and by the time we got to dessert—a blueberry cake that felt like the perfect summer finish—it was clear this wasn’t just a good meal, it was the one we kept comparing everything else to for the rest of the trip.

Need more travel inspiration, here are some of my favorites:

•  Long Beach Island in New Jersey
• Virginia’s Shenandoah Valley 
• Asheville, North Carolina
• Tilghman Island, Maryland
• Glamping in Asheboro, NC

Drooling for more? Follow me on Instagram and Facebook!